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Is it possible to establish an HTTPS connection and embed JavaMail inside of it?

It should be possible, but you'll need to write your own SocketFactory and configure JavaMail to use it. The SocketFactory will need to make the connection through the HTTP proxy server using the HTTP CONNECT protocol command, then turn the socket over to JavaMail for use. You'll probably need to write the HTTP protocol support yourself, rather than using HttpURLConnection.

Alternatively, there are some programs that act as a SOCKS proxy server and forward messages through a web proxy server. You can then use the SOCKS support in JavaMail.

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